A lake surrounded by autumn-colored trees reflecting on the water.

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middletown cottages

A rustic cabin with a stone exterior, wooden deck, and a small porch.

1. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$382 nightly
The price is $432
Nov 15 - Nov 16
Total with taxes and fees
Hello Small Stone
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$261 nightly
The price is $273
Nov 12 - Nov 13
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Nov 10 - Nov 11
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
$189 nightly
The price is $213
Nov 10 - Nov 11
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

5. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
$222 nightly
The price is $223
Nov 25 - Nov 26
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
$428 nightly
The price is $506
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A wooden deck with a white railing, surrounded by a grassy lawn and trees.

7. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.2 out of 10, Wonderful, (5 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$403 nightly
The price is $460
Nov 10 - Nov 11
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior

8. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$322 nightly
The price is $355
Nov 10 - Nov 11
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
A house with a view of a bridge and mountains.

9. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
$257 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

10. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
$457 nightly
The price is $539
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Confusing site info online as to where our room was."
Ray 1-night trip
Posted 1 hour ago
Overlook Lodge at Bear Mountain

Find out more about Middletown

Middletown Cottages information

Number of reviews
206
Accommodation
140 Cottages
Lowest Price
$213
Highest Price
$698

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What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

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